Cationic acylpyridinium derivatives for use as bleach activators

Abstract

Agent for dyeing keratin fibers while simultaneously bleaching the keratin fibers. The agent contains, in a cosmetic carrier, at least one oxidation dye precursor and at least one cationic acylpyridinium derivative.

1. Agent for dyeing and simultaneously lightening keratinic fibers comprising in a cosmetic carrier:
 at least one oxidation dye precursor, and 
 at least one cationic acylpyridinium derivative according to the following Formula (I), 
 
       
         
           
           
               
               
           
         
       
       wherein
 R1 is a C 1 -C 6  alkyl group, a C 2 -C 6  alkenyl group, a C 2 -C 6  hydroxyalkyl group, a C 1 -C 6  alkoxy C 2 -C 6  alkyl group, a carboxy C 2 -C 6  alkyl group, an aryl C 1 -C 6  alkyl group, a heteroaryl C 1 -C 6  alkyl group, an aryl group or a heteroaryl group; 
 R2 is an acyl group according to the formula R′C(O) in which R′ is a C 1 -C 6  alkyl group, a C 2 -C 6  hydroxyalkyl group, a C 1 -C 6  alkoxy C 2 -C 6  alkyl group, a carboxy C 1 -C 6  alkyl group, an aryl C 1 -C 6  alkyl group, or a heteroaryl C 1 -C 6  alkyl group; 
 R3, R4 and R5 are, independently of one another, a hydrogen atom, a hydroxyl group, an amino group, a di-(C 1 -C 6  alkyl)amino group, a C 1 -C 6  alkyl group, a C 1 -C 6  alkoxy group, a C 1 -C 6  alkoxy C 2 -C 6  alkyl group, a halogen, a nitro group, a carboxy group, a nitrile group, an optionally substituted aryl group, a C 2 -C 6  alkenyl group, an optionally substituted heteroaryl group; and 
 X −  is a physiologically acceptable anion. 
 
     
     
       2. Agent according to  claim 1  wherein R1 is a C 1 -C 6  alkyl group, a C 2 -C 6  alkenyl group, or a C 2 -C 6  hydroxyalkyl group. 
     
     
       3. Agent according to  claim 1  wherein R2 is an acyl group having the formula R′C(O), wherein R′ is a C 1 -C 6  alkyl group. 
     
     
       4. Agent according to  claim 1  wherein R2 is in the 2-position or 4-position of Formula (I). 
     
     
       5. Agent according to  claim 1  wherein R3, R4 and R5 are hydrogen. 
     
     
       6. Agent according to  claim 1  wherein X −  is a halide ion, hydrogen sulfate, ½ sulfate, p-toluene sulfonate, benzene sulfonate, or acetate. 
     
     
       7. Agent according to  claim 1  wherein the acylpyridinium derivative according to Formula (I) is chosen from 4-acetyl-1-methylpyridinium p-toluene sulfonate, 4-acetyl-1-methylpyridinium benzene sulfonate, 4-acetyl-1-methylpyridinium bromide, 4-acetyl-1-methylpyridinium chloride, 4-acetyl-1-methylpyridinium hydrogen sulfate, 4-acetyl-1-methylpyridinium acetate, 4-acetyl-1-allylpyridinium p-toluene sulfonate, 4-acetyl-1-allylpyridinium benzene sulfonate, 4-acetyl-1-allylpyridinium bromide, 4-acetyl-1-allylpyridinium chloride, 4-acetyl-1-allylpyridinium hydrogen sulfate, 4-acetyl-1-allylpyridinium acetate, 2-acetyl-1-methylpyridinium p-toluene sulfonate, 2-acetyl-1-methylpyridinium benzene sulfonate, 2-acetyl-1-methylpyridinium bromide, 2-acetyl-1-methylpyridinium chloride, 2-acetyl-1-methylpyridinium hydrogen sulfate, 2-acetyl-1-methylpyridinium acetate, 2-acetyl-1-allylpyridinium p-toluene sulfonate, 2-acetyl-1-allylpyridinium benzene sulfonate, 2-acetyl-1-allylpyridinium bromide, 2-acetyl-1-allylpyridinium chloride, 2-acetyl-1-allylpyridinium hydrogen sulfate or 2-acetyl-1-allylpyridinium acetate. 
     
     
       8. Agent according to  claim 1  wherein the acylpyridinium derivative according to Formula (I) is present in an amount of 0.01 to 15 wt. %, based on total weight of the agent. 
     
     
       9. Method for preparing an agent according to  claim 1  comprising:
 providing at least two preparations in at least two separately packaged containers, wherein at least a first container comprises a dye (A) having in a cosmetic carrier at least one oxidation dye precursor as well as at least one acylpyridinium derivative according to Formula (I), and at least a second container has an oxidizing agent preparation (B) comprising at least one oxidizing agent, and 
 blending directly prior to use the at least two preparations, thereby producing the agent. 
 
     
     
       10. Method according to  claim 9 , wherein the oxidizing agent is present in an amount of 0.5 to 12 wt. %, based on total weight of the agent. 
     
     
       11. Method according to  claim 9 , wherein the oxidizing agent of preparation (B) is at least hydrogen peroxide and/or one of its solid addition products on organic or inorganic compounds. 
     
     
       12. Agent according to  claim 1  further comprising a toxicologically harmless bleach co-activator according to Formula (II) and/or a physiologically acceptable salt thereof, 
       
         
           
           
               
               
           
         
       
       wherein
 Y is a carbonyl group, a direct bond or methylene group, 
 R1 is hydrogen, a C 1 -C 4  alkyl group, a physiologically acceptable cation or a SO 3   −  or a PO 3   2−  group, 
 R2 is an amino, a methylamino, a dimethylamino, a trimethylammonio group, phenyl, benzyl, phenoxymethyl, 1-naphthyl, 2-naphthyl, 2-, 3-, 4-toluoyl, or a R4-O—(CH 2 CH 2 O) n  group, in which R4 is a C 6 -C 20  alkyl group and n is a number greater than 15, and 
 R3 is hydrogen or an optionally branched C 1 -C 6  alkyl group, 
 with the proviso that, when Y is a carbonyl group,
 R1 is hydrogen, a C 1 -C 4  alkyl group or a physiologically acceptable cation, 
 R2 is an amino, a methylamino, a dimethylamino or a trimethylammonio group, and 
 R3 is hydrogen or an optionally branched C 1 -C 6  alkyl group, 
 
 with the proviso that, when Y is a direct bond,
 R1 is hydrogen and 
 R2 is phenyl, benzyl, phenoxymethyl, 1-naphthyl, 2-naphthyl, 2-, 3- or 4-toluoyl, and 
 R3 is hydrogen or an optionally branched C 1 -C 6  alkyl group, and 
 
 with the proviso that, when Y is a methylene group,
 R1 is a SO 3   −  or a PO 3   2−  group, 
 R2 is a R4-O—(CH 2 CH 2 O) n  group, in which R4 is a C 6 -C 20  alkyl group and n is a number greater than 15, and 
 R3 is hydrogen. 
 
 
     
     
       13. Agent according to  claim 1  having a pH of from 7 to 11. 
     
     
       14. Method for lightening keratinic fibers comprising applying an agent according to  claim 1  onto the keratinic fibers, leaving the agent on the fibers for 5 to 45 minutes, and rinsing out the agent with water or washing out the agent with a shampoo.